Evidence map›Paper›PMID 34672739›Full record

ArticleScience (New York, N.Y.)2021

General method for iron-catalyzed multicomponent radical cascades-cross-couplings.

Lei Liu, Maria Camila Aguilera, Wes Lee, Cassandra R Youshaw, Michael L Neidig, Osvaldo Gutierrez

Abstract read
In one paragraph

Article in Science (New York, N.Y.), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.

0numbers the graph read from it
0cells of the map it votes in
31citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

31 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Nickel-Catalyzed Twofold Conjunctive Coupling via Philicity-Alternating Radical Relay.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026
    Article
  5. Iron-mediated C(spTetrahedron · 2025
    Article
  6. Article
  7. Article
  8. Article
  9. Article
  10. Iron-Catalyzed Cross-Electrophile Coupling.Synlett : accounts and rapid communications in synthetic organic chemistry · 2025
    Article
  11. C(spCommunications chemistry · 2025
    Article
  12. Article
  13. Article
  14. General Alkene 1,2-Journal of the American Chemical Society · 2024
    Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

6 authors.

Lei Liu *Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.ORCID 0000-0002-1708-9246
Maria Camila Aguilera *Department of Chemistry, University of Rochester, Rochester, NY 14627, USA.ORCID 0000-0002-3388-0193
Wes LeeDepartment of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.ORCID 0000-0002-8754-6481
Cassandra R YoushawDepartment of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.ORCID 0000-0002-0430-8454
Michael L NeidigDepartment of Chemistry, University of Rochester, Rochester, NY 14627, USA.ORCID 0000-0002-2300-3867
Osvaldo GutierrezDepartment of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.ORCID 0000-0001-8151-7519

Funding

Iron-Catalyzed Cross-CouplingR01GM111480 · NIGMS · UNIVERSITY OF ROCHESTER · PI NEIDIG, MICHAEL L · 2014 to 2022
$3.1M
New Directions in Sustainable Open-Shell Radical C-C Bond Formations Enabled by Merging Modern Computational and Experimental MethodsR35GM137797 · NIGMS · UNIV OF MARYLAND, COLLEGE PARK · PI Osvaldo Gutierrez · 2020 to 2026
$2.7M
NIGMS NIH HHS R01 GM111480NIGMS NIH HHS R35 GM137797
6 · The paper itself

Abstract

Transition metal–catalyzed cross-coupling reactions are some of the most widely used methods in chemical synthesis. However, despite notable advantages of iron (Fe) as a potentially cheaper, more abundant, and less toxic transition metal catalyst, its practical application in multicomponent cross-couplings remains largely unsuccessful. We demonstrate 1,2-bis(dicyclohexylphosphino)ethane Fe–catalyzed coupling of α-boryl radicals (generated from selective radical addition to vinyl boronates) with Grignard reagents. Then, we extended the scope of these radical cascades by developing a general and broadly applicable Fe-catalyzed multicomponent annulation–cross-coupling protocol that engages a wide range of π-systems and permits the practical synthesis of cyclic fluorous compounds. Mechanistic studies are consistent with a bisarylated Fe(II) species being responsible for alkyl radical generation to initiate catalysis, while carbon-carbon bond formation proceeds between a monoarylated Fe(II) center and a transient alkyl radical.

Identifiers

PMID34672739
PMCPMC8929405

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.